There is just something about Tuscany that will always feel a little – okay a lot – magical. The rolling hills of wheat, the lush vineyards, the Medieval and Renaissance era walled cities…this central-northern state in Italy has had a pull on romantics worldwide for decades that is showing no signs of stopping. I fell in love with Tuscany in 2015, when my best friend and I were galivanting around Europe post-college. First, Siena wooed us with her perfect, winding Medieval streets and lively Piazza il Campo, then Prato called us to stay a while after the tourist madness of Florence. Now, in 2022, I am back and just as smitten. This time around we have come with family, so it’s a little less laissez-faire than seven years ago, but just as beautiful. If you are keen to step back in time to a world of siestas, macchiatos, wine, and so, so much art, then you must come to Tuscany; however, there are a few things that you should know before you go. Take it from me, these few tips will make your trip more ‘under the Tuscan sun’ and less, getting eaten alive by mosquitos in a 13th century convent.

Get off the beaten path – remember, there is more to Tuscany than Florence

Okay, so not to bag on Florence, but it is a very touristy city. When I was there in 2015 it was very hard to find affordable and tasty food, because everything was targeted at international tourists. Cost of accommodation sky rockets as well and there are lines for everything. Don’t get me wrong, I loved the art of that famous city (David is one sexy statue), but there are simply too many tourists in Florence for it to retain its Tuscan magic. If you are an art historian, definitely go to Florence, but for those who’s ideal trip consists of sitting in a piazza sipping a macchiato and listening to the lovely lilt of Italian conversations that you can’t understand, then Lucca or Prato might be more your style. Prato is very close to Florence (about 20 minutes by train), but a world away in atmosphere. It is a tiny town with little to no sightseeing, but ample grappa, cured meats, and espresso to entertain anyone craving ‘il dolce far niente’ – the sweetness of doing nothing.

Lucca strikes a bit more of a balance between sightseeing options and quiet ambiance, and is a town I would heartily recommend to almost anyone. It is big enough to have sightseeing options, but small enough to walk around easily and quiet enough to find a piazza to yourself for your summer lunch of melon and prosciutto, even in the height of the tourist season. Lucca’s walls are its real treasure though – massive Renaissance style walls that encircle the entire old town with a lovely circular park, complete with a wide tree lined path and plenty of benches for taking in the views. Lucca’s walls were added to in the 16th century over a worry that Florence would invade and then became the perfect promenade you see today in the 19th century post-Italian unification (nerd note – you can tell the difference between the Medieval walls of a place like Siena from Renaissance era ones by their size, the Medieval ones were rather thin as they did not need to repel significant cannon blasts).

Check the weather – summer can be quite warm if you aren’t used to the heat

Tuscany can get down right hot in summer (between the months of June and August), so plan your accommodation accordingly. Temperatures are routinely over 30 C/86 F during the day and have even climbed to 37 C/97 F since we’ve been here. Tuscany is also humid mostly year round (though it is the lowest in summer, but let’s be honest, not by much) so consider this when looking at temperatures. It averages about 60% humidity, which isn’t horrible for those coming from humid climates (Tuscany humidity has nothing on Malaysia), but it can be a real struggle for those used to dry heat. Also, note that most of Europe does not have screens on their windows so it can be hard to deal with the heat just by opening windows, especially in the countryside where there are more insects, such as the ever annoying mosquitos that just love to take the invitation of an open window to feast on your blood. If you are heat sensitive at all I would strongly suggest only booking accommodation that has air conditioning. Kane and I can deal without it, but we are used to the heat in the north of Australia, if you are coming from some place cold, beware.

Rent a car if you want to stay in a villa in Tuscany

Ah the romance of opening your personal villa’s window and breathing in that fresh country air…until a wasp flies into your face sending you running around the very old, very rustic villa flapping your hands like a deranged bat. Villas in Tuscany are beautiful. They are alluring. But, and this is the key, villas are – mostly – very old buildings rather a long way into the countryside. Italian buses are unreliable at best and your only option to get into town for supplies or just an afternoon macchiato will be taxis, which are not cheap. So, I’d suggest that, unless you are renting a car, staying within walking distance of the city centre of these smaller towns is really the best option.

Use the Trainline App for less stressful travel

Trains are the lifeblood of the European continent and Italy is no exception. Most of your intra-country travel will be on trains as the distances are just too small for flights so you need to figure out how to navigate this system with relative ease. Buying tickets at the train station can be exceptionally slow, not due to lines (most of the time), but due to the painfully lethargic ticket machines that really, really like to contemplate every change of screen for at least a minute or so before moving on to the sixth screen you need to click through to buy your ticket. We have missed trains due to these machines and I would highly recommend that, for any larger journey than say moving between the towns of the Cinque Terre, you buy your tickets in advance using the Trainline app. It does not cost more, everything is translatable to English, and you can even track your trains on the app to help you know when to get off and about any delays that are occurring (delays are common in our experience).

Don’t tip all the time, but do check for a coperto

As an American living in Australia, I have come to love the fact that tipping is not customary once you get far enough away from the USA. In countries where staff get paid well there is no need for the customer to tip in any sort of obligatory way (in the USA if you don’t at least tip 10-15% your waiter will consider you the scum of the earth). Italy falls somewhere between Australia (almost never tip) and America (always tip) in the tipping customs. We’ve had this confirmed by local friends of ours who say that, one, you definitely do not need to tip all the time, as most restaurants will charge a coperto (cover charge) anyway, and two, that if you do get really, really good service and want to tip that you must give it directly to the person you want to tip, otherwise it just goes back to the restaurant owner. Even in the second case, where you’ve had really good service 10% is plenty to tip in these instances. Also, one last note on the coperto – sometimes the menu will say in fine print how much it will be, other times you only learn how much the coperto is once you get the bill, but it varies from one euro per person in smaller establishments to a few euros per person in a big city, tourist area. The coperto covers the bread they give you at the start of the meal, but that’s about it, still expect to pay for everything else, including water.

Share dishes when eating out to get a balanced meal

Italians seem to have a moral aversion to combining meat, carbs, and vegetables in the same dish. Chicken with pesto pasta and vegetables in one dish? It is impossible, and, quite possibly sacrilegious in Italy; okay I’m being a bit dramatic on this, but when you order a meat dish (often found in the secondi section), do not expect anything more than meat. The same goes for your pastas, which are found in the primi section, and any side dishes, found in the contorni section. Despite what you may have read online, most Italians do not order a primi, secondi, and contorni, it would just be way too much food. Instead, sharing dishes is very common here, so common that if two of you order the same dish they will often bring it in one big bowl to share. Kane and I have had no issues ordering a primi and a secondi to share between the two of us for our whole time in Italy, it’s pretty much the only way to get protein and pasta at the same time.

Go to Siena, just not during Palio time, unless you love crowds

Oh Siena, the magical Medieval city that started my love affair with Tuscany. This is a beautiful town south of Florence that has so much going for it, from the stunning Duomo to the hilly cobblestones streets filled to the brim with enotecas (wine shops) and gelaterias. My favourite time of day in Siena is just after sunset, which is around 8:30 pm in summer, sitting in the Piazza il Campo and watching the swifts that live in the bell towers dance across the sky while locals and tourists alike relax on the brick Piazza like they are lounging at the beach. However, Siena is known around the world for something a bit more hair raising than dodging swift poop while snacking on your evening gelato – the Palio. The Palio is a famous horse race that has all the contradas dressed up in their best Medieval finery cheering their neighborhood’s horse to a hopeful victory after three mad laps around the Piazza with a jockey clinging on sans saddle.

When I first traveled to Siena it was well outside of Palio time, and while there was a lot to learn about the contradas and their fiercely local spirits, it was still mostly a quiet, smaller town. Yes, there were tourists, but there were locals too and pretty much no waits for anything. This latest trip to Siena was a bit different though, as we went about a week and a half before the first run of the Palio (they run the race twice a year, once in early July and once in early August). Our first couple of nights in the city were the slow magic that I had remembered, but when the clock started ticking down to 8 days before Palio, 7 days before Palio, the city erupted. The first signs of the change where the contrada bands and flag throwers practising in the streets – when you hear those drums, follow the sound for an entertaining sneak peak of what is to come in the following week. Then, a week before the race they started packing tons and tons of dirt into the path around the Piazza il Campo and overnight it goes from a cobblestone path for meandering to a race track fit for a mad man. They even put mattresses up along the narrower sides to protect both the shop fronts and the race participants from the inventible falls that come with racing bareback. Finally, the crowds of tourists and locals alike descend on Siena in the week leading up to the Palio, making previously relaxed streets almost impassable in places. One final note, the Palio is very much for the locals, so if you choose to go, please be respectful of what this event means to them, it is the most important event of the year.

We considered staying to see the race, but after looking up how much it would cost to get any view that wasn’t crammed into the center of the Piazza for five hours with negative personal space, we decided it wasn’t for us. I’m not a fan of crowds on a good day and, for me, a huge part of the magic of Siena its leisurely pace – which changes completely come Palio. If you love pageantry, neighbourhood rivalries, and can stand serious crowds, then come to Siena during Palio time and tell me how it is, I’m keen to hear. If crowds, lines, and expensive everything isn’t your cup of tea, then do as we did and avoid the area for at least a week before Palio time.

Stay elsewhere and day trip to big tourist sites

Given it’s my second time in Tuscany and we were staying in Lucca, I thought it was high time that I see Pisa. Yes, I’d heard it before, the leaning tower of Pisa is mostly a glorified tour bus photo op, but I wanted to see it for myself. However, I didn’t want to waste a whole day on a disappointing destination without at least enjoying the journey so we hired e-bikes in Lucca and rode to Pisa. Our path wound along the Serchio River, through Tuscan farmland, and over some rather bumpy gravel/rocky roads (maybe get the mountain e-bike next time) and it was hands down the best way to see Pisa, because we got to spend a lovely day in the countryside, stop in at tourist mayhem, see the tower, then run away back to the countryside. It cost us 35 euro each for the day of e-bike hire and took us about 4 1/2 hours all up, you could do it on a normal bike for less money, but I would double the time needed to get there and back (it’s about a 50 km round trip and you need to budget time for getting lost). You don’t need to ride a bike to get to Pisa from Lucca, there is a train that is cheap and quick, but whatever you do, I would recommend making places like Pisa a day trip rather than a multi-day stay to avoid expensive accommodation, food, etc.

Learn a little Italian, especially if you’re heading to smaller towns

In the big cities and main tourist attractions it’s a safe bet that most people will speak at least a little English, however, this bet gets significantly longer odds the further you go into the countryside of Tuscany. I know it can be hard to learn another language just for a trip, but a few buongiorno’s, grazie’s, and buonasera’s go a long way towards ingratiating yourself to the locals and it shows respect of their culture and language. The words we have used the most are as follows:

• Buongiorno – good morning, use this until about 1/2 pm
• Buonasera – good afternoon, safe to use anytime after 1 pm and you can use it well into the night
• Buonanotte – good night. This is really only used for saying good bye at night, like if you are walking into your hotel room for the evening you can say buonanotte to the reception staff
• Un tavolo per due, per favore – A table for two, please. Use this at restaurants and do not forget to say per favore, you will be rude if you don’t. Swap the number for however many people you have in your group (uno – 1, due – 2, tre – 3, quattro – 4, cinque – 5, sei – 6, sette – 7, otto – 8, nove – 9, dieci – 10)
• Vorrei… – I would like… Use this for ordering and follow with what you would like, if you are struggling with pronunciation double up by pointing at what you want on the menu while you are trying to say it in Italian. They appreciate the effort, but sometimes our Anglo-pronunciations are atrocious and the pointing helps to avoid culinary confusion.
• Mi scusi – Excuse me. Scusi is a very versatile Italian word and can help you, politely, get the attention of waitstaff, move around people in a crowd, or ask strangers for directions.
• il conto, per favore – The bill, please. Unless you are eating at a real fast food type of place (like a pizza by the slice joint where you eat standing up), you will need to ask for the bill. Italian waitstaff consider it rude to bring you the bill without you asking first, so don’t just wait for them to bring it like you would in America, you need to ask. If you can’t speak to them because it’s too crowded, catching their eye and doing the universal air scribble, while mouthing ‘il conto, per favore’ mostly does the trick too.

Don’t rush it, enjoy the pace of life in Tuscany

Tuscany, and Italy as a whole, is about ‘il dolce far niente’ so don’t rush your trip here. Spend at least three nights anywhere you stay so you aren’t constantly dealing with the stress of moving around and, if you have the vacation time, try to spend a good chunk of time in a single location (I would say a week) to really get a feel for the place and to unwind into the culture. I know this can be hard for Americans given the paltry amount of vacation days most people get, but even with say, only ten days to travel, you can manage to avoid the frantic rush-rush by limiting yourself to no more than three destinations (I would even say two would be better than three if you only have ten days, but I know the concept of slow travel can be hard for some to embrace).

Whatever you do, enjoy your time in Tuscany, it is a beautiful area of the world that will always make my romantic soul sing – oh and you must enjoy the food and wine, but that is obvious to anyone traveling Italy. I strongly recommend Sangiovese (Brunello, Montepulcianos, Montalcinos, etc.) and focaccia (you will never look at bread the same way again).